Devilfish

If you've never eaten Octopus and it's never made it very high on your list of "I've got to try it", the best way to make sure you never will is to watch the first 10 minutes or so of the Iron Chef (Japanese Version) Octopus Challenge.  The octopus is a very strange creature without many parallels out there, perhaps the closest being the squid, but who hasn't had calamari?  And how often do you have the opportunity to eat something that was once called a devilfish, no doubt part due to its common presence as a sea monster in the stories of ocean explorers.  

Octopus is one of those foods that, in my experience, can be very good or mediocre.  My first experience with octopus, as sushi (or Tako) was on the mediocre side of things.  It was tough and rubbery and ended up as a plaything for the neighbor's cat... literally.  

But as with many dishes, don't let a bad example spoil it for you.  Since then I've had incredible preparations of octopus in both simple and complex dishes.  My favorites by far have been very simple Italian preparations of octopus.  When properly prepared, the octopus is simple, flavorful, and very tender.  This is definitely a dish to try at a respectable restaurant.  Freshness and preparation will determine whether it's enjoyable.  And if you get a good example, it's ultimately not at all challenging.  You will likely find yourself taking a bit to try it and then rushing back for a larger scoop before it's all gone.